Imido carbonate compound, production thereof and uses thereof as reagent for forming active ester of amino acids

Abstract

A new carbonate compound which is N,N'-di-succinimidyl carbonate, N,N'-diphthalimidyl carbonate or N,N'-bis(5-norbornene-2,3-dicarboxyimidyl) carbonate is produced by reacting an N-hydroxy compound of the formula R-OH wherein R is succinimido, phthalimido or 5-norbornene-2,3-dicarboximido group, with a silylating agent, followed by reacting the resultant silylated product with phosgene, or alternatively by reacting said N-hydroxy compound with trichloromethyl chloroformate either in the molten state or in the presence of a non-polar organic solvent such as xylene. This new carbonate compound is useful not only as a reagent for forming active esters from amino acid but also as a reagent for introducing a carbonyl group between a pair of amino groups, a pair of amino and hydroxyl groups or a pair of amino and mercapto groups, for producing an isothiocyanate from a dithicarbamic acid by removal of hydrogen sulfide from the latter, and for producing acrylic acid derivatives from N-protected serine by dehydration of the latter.

What we claim is: 
     
       1. A carbonate compound of the formula (I) ##STR83## wherein R represents a succinimido, phthalimido or 5-norbornene-2,3-dicarboximido group. 
     
     
       2. The carbonate compound of claim 1 which is N,N'-disuccinimidyl carbonate. 
     
     
       3. The carbonate compound of claim 1 which is N,N'-diphthalimidyl carbonate. 
     
     
       4. The carbonate compound of claim 1 which is N,N'-bis (5-norbornene-2,3-dicarboximidyl) carbonate.